Dimethyl Sulfoxide → 5,8-Dihydro-1-naphthyl benzyl ether

HRID 267559

반응식

HRID 267559 반응식
[C:1]1([OH:11])[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.CS(C)=O.C[O-].[Na+].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([O:11][C:1]1[C:10]2[CH2:9][CH:8]=[CH:7][CH2:6][C:5]=2[CH:4]=[CH:3][CH:2]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 974665,8-Dihydro-1-naphtholHCID 10942334Sodium Methoxide

생성물 1

HCID 203605175,8-Dihydro-1-naphthyl benzyl ether

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A solution of 73 g. (0.5 m) of 5,8-dihydro-1-naphthol in 100 ml. DMSO is treated with 0.5 m sodium methoxide. The mixture is cooled in an ice bath and treated dropwise with 0.5 mole benzyl bromide with shaking periodically. The mixture is gradually allowed to warm up to about 45° toward the end of addition. The mixture is stirred 3 hrs. longer, then poured into 1 liter H2O and extracted into ether. Extracts are washed twice with 10% NaOH, dried, taken to dryness leaving almost a quantitative yield of crystalline 5,8-dihydro-1-naphthyl benzyl ether.

후처리

  1. temperatureThe mixture is cooled in an ice bath
  2. temperatureto warm up to about 45° toward the end of addition
  3. stirringThe mixture is stirred 3 hrs
  4. extractionextracted into ether
  5. washExtracts are washed twice with 10% NaOH
  6. customdried

출처 및 근거

ORD 기록
ord-9758e78849c448b5a32ec211e23ab811
출처 데이터셋
uspto-grants-1976_03
특허 번호
US03943149

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